Selenides of heterocyclic amines



Patented Oct. 5, 1954 UNITED STATES PATENT OFFICE SELENIDES F HETEROCYCLIC AMINES Chester W. Christensen, Akron, Ohio, assignor to Monsanto Chemical Company, St. Louis, Mo., a corporation of Delaware No Drawing. Application August 16. 1951, Serial No. 242,189

3 Claims. 1

EIQALEPLE To a suitable reaction vessel containing 8'7 parts by weight (substantially 1 mole) of morpholine dissolved in 352 parts by weight of benzene is added with agitation a solution containing 57.2 parts by weight (substantially 0.25 mole) of commercial selenium monochloride dissolved in 88 parts by weight of benzene while maintaining the temperature at to +10 C. Upon completion of the addition of the selenium monochloride the reaction mix is agitated for one hour while maintaining the temperature at about 0 C. The reaction mix is filtered and the filtrate evaporated yielding 20.6 parts by weight of a selenide of morpholine as a brick-red solid possessing a melting point of 90-95 C. Analysis indicated the product was essentially N,N-triseleno-bis-morpholine. For example nitrogen found was 6.57% and 6.82% as compared to a calculated value of 6.84% for the triselenide.

Employing substantially the same reaction conditions the N,Nselenides of pyrrolidine, piperidine, and 04-, 3-, and v-pipecoline are prepared by replacing morpholine with an equimolar amount, respectively, of pyrrolidine, piperidine, and oc-, [3-, and -pipecoline.

In the preparation of the new compounds of this invention other selenium halides than the chlorides may be employed, for example selenium monobromide, selenium monoiodide, selenium tetrabromide, and the like.

The new compounds are useful as fast-curing vulcanization agents in the production of vulcanizates having low moduli and as illustrative 2 thereof the following rubber stock is compounded in the usual manner:

Parts by weight Smoked sheets rubber 100 Carbon black Zinc oxide 5 Stearic acid 3 Saturated hydrocarbon oil 2 p-Amino biphenyl-acetone condensation product 1.5 N-cyclohexyl benzothiazole sulfenamide--- 0.8 N,N-di-seleno-bis-morphcline 1.9

The above stock so compounded is vulcanized 1n the usual manner by heating in a press at 144 C. The physical properties of the 30 minute cure are set forth below:

Table tMotdulus1 boil Elasmum t ici y in s. in! at a e Elongations of- E .22 5? Elongaation, perlbs/1n. cent 300% 500% References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 2,433,179 Wheeler Dec. 23, 194? OTHER REFERENCES Kaufman: Chemical Abstracts, vol. 20, p. 1364 Binz: J. Am. Chem. 300., January 1940, pp. 7 and 8. 

1. AS A NEW COMPOSITION OF MATTER N,N''-TRISELENO-BIS-MORPHOLINE. 